KR860002456A - 치환된 카보디이미드의 제조방법 - Google Patents
치환된 카보디이미드의 제조방법 Download PDFInfo
- Publication number
- KR860002456A KR860002456A KR1019850006812A KR850006812A KR860002456A KR 860002456 A KR860002456 A KR 860002456A KR 1019850006812 A KR1019850006812 A KR 1019850006812A KR 850006812 A KR850006812 A KR 850006812A KR 860002456 A KR860002456 A KR 860002456A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- compound
- substituted
- halogen
- chlorine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 11
- 150000001718 carbodiimides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 229910052801 chlorine Inorganic materials 0.000 claims 12
- 239000000460 chlorine Substances 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- -1 di-substituted phenoxy Chemical group 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000005554 pyridyloxy group Chemical group 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C267/00—Carbodiimides
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Saccharide Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (14)
- 일반식(Ⅱ)의 화합물로부터 물 또는 황화수소를 제거시킴을 특징으로 하여, 일반식(Ⅰ)의 치환된 N-페닐-N′-알킬카보디이미드를 제조하는 방법.상기식에서, R1은 수소, 할로겐, C1-C10알킬 또는 C1-C5알콕시이거나, 1 내지 7개의 할로겐원자로 치환된 C1-C5알콕시이거나, 또는 C1-C5알킬티오이며; R2는 수소, 할로겐, C1-C10알킬 또는 C1-C5알콕시이고; R3은 수소, C1-C10알킬, 할로겐, 페녹시 또는 페닐티오이거나, 할로겐, 메틸, 에틸, 1 내지 7개의 할로겐 원자를 함유하는 C1-C3할로알킬 및 시아노로 이루어진 그룹중에서 선택된 치환체로 각각 일치환 되거나 이치환된 페녹시 또는 페닐티오이거나, 피리딜옥시 또는 할로겐 및 1 내지 7개의 할로겐 원자를 함유하는 C1-C3할로알킬로 구성된 그룹중에서 선택된 치환체로 일치환거나나 이치환된 피리딜옥시이며; R4는 C1-C12알킬, 총탄소수 2 내지 10의 알콕시알킬 C3-C10사이클로알킬, C3-C10사이클로알킬메틸, 또는 1 내지 3개의 C1-C2알킬그룹으로 치환된 C3-C10사이클로알킬이거나, 1 또는 2개의 C3-C10사이클로알킬 그룹으로 치환된 C1-C5알킬이거나, 탄소수 7 내지 10의 폴리사이클릭 알킬그룹, 페닐(C1-C5)알킬, 또는 페닐핵에서 할로겐, 트리플루오로메틸, 메톡시 또는 에톡시로 일치환되거나 이치환된 페닐(C1-C5)알킬이고; X는 산소 또는 황이다.
- 제1항에 있어서, R1이 수소, 할로겐, C1-C10알킬 또는 C1-C5알콕시이거나, 1 내지 7개의 할로겐원자로 치환된 C1-C5알콕시이거나, 또는 C1-C5알킬티오이며; R2가 수소, 할로겐, C1-C10알킬 또는 C1-C5알콕시이고; R3가 수소, C1-C10알킬, 할로겐, 페녹시 또는 할로겐, 트리루오로메틸 및 시아노로 구성된 그룹중에서 선택된 치환체로 일치환 되거나 이치환된 페녹시이거나, 페닐티오, 피리딜옥시, 또는 할로겐 및 트리플루오로메틸로 구성된 그룹중에서 선택된 치환체로 일치환되거나 이치환된 피리딜옥시이며; R4가 C1-C10알킬, 총탄소수 2 내지 10의 알콕시알킬, C3-C10사이클로알킬, C3-C10사이클로알킬메틸, 또는 C1-C3알킬그룹으로 치환된 C3-C10사이클로알킬인 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 제1항에 있어서, R1이 수소, 불소, 염소, C1-C4알킬, 메톡시, 에톡시, 트리플루오로메톡시 또는 C1-C3알킬티오이며; R2은 수소, 불소, 염소, C1-C4알킬, 메톡시 또는 에톡시이고; R3가 수소, C1-C4알킬, 불소, 염소, 페녹시 또는 페닐티오이거나, 염소 및/또는 트리플루오로메틸로 일치환 되거나 이치환된 페녹시이거나, 피리딜옥시, 또는 불소, 염소 및 트리플루오로메틸로 구성된 그룹중에서 선택된 치환체로 일치환되거나, 이치환된 피리딜옥시이며; R4가 C1-C8알킬, 총탄소수 2 내지 7의 알콕시알킬, C3-C8사이크로알킬, C3-C8사이클로알킬메틸, 메틸(C3-C6) 사이클로알킬, 페닐(C1-C4) 알킬, 또는 페닐핵에서 염소, 트리플루오로메틸 또는 메톡시로 일치환되거나 이치환된 페닐(C1-C4) 알킬인 일반식(Ⅰ)의 화합물로 제조하는 방법.
- 제3항에 있어서, R1이 수소, 불소, 염소, C2-C4알킬, 메톡시이며; R2가 수소, 염소, C3-C4알킬 또는 메톡시이고; R3가 메틸, 에틸, 이소프로필, 염소 또는 페녹시이거나 염소 및/또는 트리플루오로메틸로 일치환되거나 이치환된 페녹시이거나, 피리딜옥시, 또는 염소 및/또는 트리플루오로메틸 일치환되거나 이치환된 피리딜옥시이며; R4가 C3-C8알킬, C1-C4알콕시(C1-C3)-알킬, C3-C6사이클로알킬, 페닐(C1-C4)알킬, 또는 페닐핵에서 염소원자 또는 메톡시 그룹으로 치환된 페닐(C1-C4) 알킬인 일반식(Ⅰ)의 화합물로 제조하는 방법.
- 제1항 내지 4항중 어느 하나에 있어서, 래디칼 R1,R2및 R3중의 하나가 4-위치에 존재하고, 나머지 두개의 래디칼이 서로 독립적으로 2-및 6-위치에 존재하는 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 제1항 내지 5항중 어느 하나에 있어서, R4가 이소프로필 또는 3급-부틸인 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 제1항 내지 6항중 어느 하나에 잇어서, R1및 R2가 2-및 6-위치에 존재하는 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 제4항에 있어서, 제조된 화합물이 다음 구조식의 화합물인 방법.
- 제4항에 있어서, 제조된 화합물이 다음 구조식의 화합물인 방법.
- 제4항에 있어서, 제조된 화합물이 다음 구조식의 화합물인 방법.
- 제4항에 있어서, 제조된 화합물이 다음 구조식의 화합물인 방법.
- 제4항에 있어서, 제조된 화합물이 다음 구조식의 화합물인 방법.
- 제3항에 있어서, 제조된 화합물이 다음 구조식의 화합물인 방법.
- 제4항에 있어서, 제조된 화합물이 다음 구조식의 화합물인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH447984 | 1984-09-19 | ||
CH4479/84-9 | 1984-09-19 | ||
CH3526/85-5 | 1985-08-15 | ||
CH3526/85 | 1985-08-15 | ||
CH352685 | 1985-08-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR860002456A true KR860002456A (ko) | 1986-04-26 |
KR900008135B1 KR900008135B1 (ko) | 1990-10-31 |
Family
ID=25693241
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019850006812A KR900008135B1 (ko) | 1984-09-19 | 1985-09-18 | 치환된 카보디이미드의 제조방법 |
Country Status (20)
Country | Link |
---|---|
US (2) | US4812466A (ko) |
EP (1) | EP0175649B1 (ko) |
KR (1) | KR900008135B1 (ko) |
AT (1) | ATE59633T1 (ko) |
AU (1) | AU587202B2 (ko) |
BR (1) | BR8504542A (ko) |
CA (1) | CA1234120A (ko) |
DE (1) | DE3581029D1 (ko) |
DK (1) | DK422785A (ko) |
EG (1) | EG18352A (ko) |
ES (1) | ES8702346A1 (ko) |
GB (1) | GB2164936B (ko) |
HU (1) | HU199403B (ko) |
IE (1) | IE58092B1 (ko) |
IL (1) | IL76381A (ko) |
MY (1) | MY101328A (ko) |
NZ (1) | NZ213522A (ko) |
PH (1) | PH21233A (ko) |
TR (1) | TR22826A (ko) |
ZW (1) | ZW15785A1 (ko) |
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Publication number | Priority date | Publication date | Assignee | Title |
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US4965389A (en) * | 1987-03-10 | 1990-10-23 | Ciba-Geigy Corporation | Phenoxyphenylthioureas phenoxyphenylisothioureas and phenoxyphenylcarbodiimides and use thereof for controlling pests |
US4897424A (en) * | 1987-06-18 | 1990-01-30 | Ciba-Geigy Corporation | Aryloxyphenylthioureas, aryloxyphenylisothioureas and aryloxyphenylcarbodiimides and pesticidal compositions containing them |
EG18799A (en) * | 1987-08-20 | 1994-02-28 | Ciba Geigy Ag | Phenylthioureas, phenylisothioureas and phenylcarbodumides their preparation and use in the control of pests |
US5026730A (en) * | 1987-08-21 | 1991-06-25 | Ciba-Geigy Corporation | Anilinophenylthioureas, compositions containing them, and the use thereof in pest control |
US4918230A (en) * | 1988-06-14 | 1990-04-17 | Ciba-Geigy Corporation | Process for the preparation 4-bromoaniline hydrobromides |
EP0407346A3 (en) * | 1989-07-07 | 1991-10-02 | Ciba-Geigy Ag | Aminopyridines |
KR920007993A (ko) * | 1990-10-18 | 1992-05-27 | 베르너 발데크 | 디페닐에테르 유도체와 그의 제조 방법 |
EP0736252A3 (en) * | 1995-04-05 | 1997-05-02 | Ciba Geigy Ag | Synergistic compositions with diafanthiuron |
ZA965805B (en) * | 1995-07-10 | 1997-01-10 | Ciba Geigy A G A Legal Body Or | Pesticide |
TW361995B (en) * | 1995-07-10 | 1999-06-21 | Novartis Ag | Pesticidal composition |
IL153360A0 (en) | 2000-06-16 | 2003-07-06 | Hercules Inc | Chemically-modified peptides, compositions, and methods of production and use |
US6479438B2 (en) * | 2001-01-04 | 2002-11-12 | Isp Investments Inc. | Gel inhibited liquid carrier for a biocide containing a carbodiimide and an emulsifier mixture |
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US2942025A (en) * | 1958-05-19 | 1960-06-21 | Gen Aniline & Film Corp | Process for producing carbodiimides |
BE610280A (ko) * | 1960-11-15 | |||
DE1149712B (de) * | 1961-11-14 | 1963-06-06 | Bayer Ag | Verfahren zur Herstellung von Carbodiimiden |
US3781357A (en) * | 1962-03-08 | 1973-12-25 | Ciba Geigy Ag | Alkylphenyl-and chlorophenoxy-phenyl-formamidines |
US3301895A (en) * | 1963-01-31 | 1967-01-31 | Upjohn Co | Process for the preparation of carbodiimides |
US3230068A (en) * | 1963-07-26 | 1966-01-18 | Du Pont | Method for retarding the growth of crabgrass |
US3621100A (en) * | 1965-11-18 | 1971-11-16 | Geigy Chem Corp | Composition and method for producing a tuberculostatic effect |
US4056631A (en) * | 1973-10-23 | 1977-11-01 | Showa Denko K.K. | Method of combatting ticks |
NL7315350A (nl) * | 1973-11-09 | 1975-05-13 | Akzo Nv | Nieuwe aminoguanidine verbindingen. |
US4101675A (en) * | 1973-11-09 | 1978-07-18 | Akzona Incorporated | Novel 2,6-di-substituted phenyl-aminoquanidine containing compositions and methods of using same and pharmaceutical compositions containing the same and therapeutic method |
US3972933A (en) * | 1974-05-28 | 1976-08-03 | Monsanto Company | Preparation of carbodiimides from ureas by dehydration |
GB1476086A (en) * | 1975-03-26 | 1977-06-10 | Showa Denko Kk | Substituted carbodiimides and pesticidal compositions thereof |
DE2553259A1 (de) * | 1975-11-27 | 1977-06-02 | Bayer Ag | Ektoparasitizide mittel enthaltend diphenylcarbodiimide und ammoniumsalze |
EP0109211A1 (en) * | 1982-11-05 | 1984-05-23 | Imperial Chemical Industries Plc | Pyridine derivatives |
US4537620A (en) * | 1984-07-02 | 1985-08-27 | Stauffer Chemical Company | Aryloxyphenoxy proponyl isothioureas and use as herbicides |
-
1985
- 1985-09-13 IL IL76381A patent/IL76381A/xx not_active IP Right Cessation
- 1985-09-13 EP EP85810416A patent/EP0175649B1/de not_active Expired - Lifetime
- 1985-09-13 AT AT85810416T patent/ATE59633T1/de not_active IP Right Cessation
- 1985-09-13 DE DE8585810416T patent/DE3581029D1/de not_active Expired - Lifetime
- 1985-09-17 CA CA000490869A patent/CA1234120A/en not_active Expired
- 1985-09-17 GB GB08522914A patent/GB2164936B/en not_active Expired
- 1985-09-18 AU AU47568/85A patent/AU587202B2/en not_active Ceased
- 1985-09-18 KR KR1019850006812A patent/KR900008135B1/ko not_active IP Right Cessation
- 1985-09-18 HU HU853518A patent/HU199403B/hu not_active IP Right Cessation
- 1985-09-18 ES ES547071A patent/ES8702346A1/es not_active Expired
- 1985-09-18 EG EG591/85A patent/EG18352A/xx active
- 1985-09-18 NZ NZ213522A patent/NZ213522A/xx unknown
- 1985-09-18 ZW ZW157/85A patent/ZW15785A1/xx unknown
- 1985-09-18 IE IE230685A patent/IE58092B1/en not_active IP Right Cessation
- 1985-09-18 PH PH32804A patent/PH21233A/en unknown
- 1985-09-18 BR BR8504542A patent/BR8504542A/pt not_active IP Right Cessation
- 1985-09-18 DK DK422785A patent/DK422785A/da not_active Application Discontinuation
- 1985-09-19 TR TR38683/85A patent/TR22826A/xx unknown
-
1987
- 1987-08-10 MY MYPI87001271A patent/MY101328A/en unknown
- 1987-10-26 US US07/115,633 patent/US4812466A/en not_active Expired - Fee Related
-
1988
- 1988-12-22 US US07/288,396 patent/US4921876A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0175649B1 (de) | 1991-01-02 |
CA1234120A (en) | 1988-03-15 |
ES8702346A1 (es) | 1987-01-01 |
NZ213522A (en) | 1989-05-29 |
US4812466A (en) | 1989-03-14 |
ATE59633T1 (de) | 1991-01-15 |
AU587202B2 (en) | 1989-08-10 |
HUT38301A (en) | 1986-05-28 |
EG18352A (en) | 1992-04-30 |
HU199403B (en) | 1990-02-28 |
EP0175649A2 (de) | 1986-03-26 |
PH21233A (en) | 1987-08-21 |
IE58092B1 (en) | 1993-06-30 |
US4921876A (en) | 1990-05-01 |
GB8522914D0 (en) | 1985-10-23 |
ES547071A0 (es) | 1987-01-01 |
IL76381A0 (en) | 1986-01-31 |
MY101328A (en) | 1991-09-05 |
DK422785A (da) | 1986-03-20 |
IE852306L (en) | 1986-03-19 |
GB2164936A (en) | 1986-04-03 |
AU4756885A (en) | 1986-03-27 |
DK422785D0 (da) | 1985-09-18 |
BR8504542A (pt) | 1986-07-15 |
KR900008135B1 (ko) | 1990-10-31 |
IL76381A (en) | 1991-06-10 |
EP0175649A3 (en) | 1987-01-14 |
TR22826A (tr) | 1988-08-17 |
ZW15785A1 (en) | 1986-04-16 |
GB2164936B (en) | 1989-01-11 |
DE3581029D1 (de) | 1991-02-07 |
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